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$89+ Cheap flights from Pensacola (PNS) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Jun 4 — Jun 111
Wed 6/4
Wed 6/11
1 adult, Economy
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Cheap flight deals from Pensacola to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Pensacola (PNS) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$224
(Southwest)

One-way from

$89
(Southwest)

Popular in

July

Cheapest in

May

Average price

$216

Good round-trip deal

$227 or less

Good one-way deal

$136 or less
Provider with most accurate pricing for Pensacola-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Pensacola-Chicago Midway flights.
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From Pensacola to Chicago Midway
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One-way flight from Pensacola to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Pensacola to Chicago Midway.
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Price to beat on a one-way flight from Pensacola to Chicago Midway.
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Find flight deals from Pensacola to Midway

Cheapest flights from Pensacola to Midway
Explore the most affordable flight options available from Pensacola to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 30, 2025.

This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/66:30 pmPNS - MDW
1 stop4h 50mSouthwest
Mon 8/1110:15 amMDW - PNS
1 stop4h 20mSouthwest
Deal found 5/29$224
This Booking.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/134:29 pmPNS - MDW
1 stop28h 24mFrontier
Sun 6/152:44 pmMDW - PNS
1 stop24h 45mFrontier
Deal found 5/29$292
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/73:35 pmPNS - MDW
1 stop6h 09mDelta
Fri 10/1010:35 amMDW - PNS
1 stop3h 48mDelta
Deal found 5/29$307
This Mytrip deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/216:00 amPNS - MDW
3 stops28h 55mMultiple Airlines
Mon 6/231:41 pmMDW - PNS
2 stops8h 56mMultiple Airlines
Deal found 5/29$535

Cheapflights Fare Finder

Customize your flight search to find flights from Pensacola to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 30, 2025.
Use the filters below to find and compare flights from Pensacola to Chicago Midway Airport that are best for you.

Fly from

Pensacola

Fly to

Midway

Route

Depart

Return

Price

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 8/6

6:30 pm-11:20 pm

1 stop4h 50m

Chicago Midway

Mon 8/11

10:15 am-2:35 pm

1 stop4h 20m

$224

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 6/13

4:29 pm-8:53 pm

1 stop28h 24m

Chicago Midway

Sun 6/15

2:44 pm-3:29 pm

1 stop24h 45m

$292

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 10/7

3:35 pm-9:44 pm

1 stop6h 09m

Chicago Midway

Fri 10/10

10:35 am-2:23 pm

1 stop3h 48m

$307

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 6/21

6:00 am-10:55 am

3 stops28h 55m

Chicago Midway

Mon 6/23

1:41 pm-10:37 pm

2 stops8h 56m

$535

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 7/8

9:35 am-11:50 am

Nonstop2h 15m

$89

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 7/23

4:37 pm-9:42 pm

1 stop5h 05m

$99

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 9/13

4:35 pm-7:01 pm

1 stop26h 26m

$118

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sun 10/5

8:46 am-4:33 pm

2 stops31h 47m

$165

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/29

Compare providers for flights from Pensacola to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pensacola to Midway in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Pensacola-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pensacola-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pensacola-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pensacola-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pensacola-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Pensacola to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pensacola with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Pensacola to Chicago Midway Airport

What is the cheapest month to book a flight from Pensacola to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Pensacola to Chicago Midway Airport (average of $160). Flying from Pensacola to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PNS to MDW?

Find hourly flight availability from Pensacola to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 30, 2025.

One of the essential ways to save on airfare from Pensacola to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 8% on airfare.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated May 30, 2025.
Read reviews from past customers who have flown Southwest, Delta and Frontier from Pensacola to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,952 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
6.0
Okay
3,288 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Pensacola to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Pensacola to Chicago Midway?

    Located just 4.0 mi from the city center, Pensacola is the airport most travelers will use when flying to Chicago Midway from Pensacola. Booking flights from Pensacola (PNS) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 2 different airlines.

  • What are the cheapest airlines flying from Pensacola to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Pensacola to Chicago Midway Airport round-trip from $224. Other airlines that can offer you cheap pricing are Frontier, from $292, and Delta, from $307. These flights start at 37% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Pensacola to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Pensacola to Chicago Midway Airport are Southwest ($89), Delta ($99), and Frontier ($118).

  • What are the cheapest flights from Pensacola to Chicago Midway Airport?

    The cheapest flight price from Pensacola to Chicago Midway Airport is $88. On average you can expect to pay $238. The most popular route, (Pensacola - Chicago Midway), can usually be booked for $197.

  • Can I find deals for flights from Pensacola to Midway that include hotel bookings?

    Yes. In addition to deals on Pensacola to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pensacola to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pensacola to Midway.

  • Can I find deals for business class flights from Pensacola to Midway?

    Yes. Cheapflights offers flight deals from Pensacola to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pensacola to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Pensacola to Chicago Midway Airport (average of $160). Flying from Pensacola to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 2 airlines flying from Pensacola to Midway

Discover the top 2 airlines that operate flights from Pensacola to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$334FlexibilityNo cancel feeOn-time63%
DeltaCheapest$228Average$358FlexibilityNo cancel feeOn-timeN/A

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